Sodium Hydroxide → HCID 10814358, compound

HRID 2396761Notes

Reaction equation

HRID 2396761 reaction equation
[N:1]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][CH2:24][C@H:2]1[C:3]([NH:5][C@@H:6]([C:12]([NH:14][C@H:15]([C:20]([O:22]C)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[C:7]([S:10][CH3:11])([CH3:9])[CH3:8])=[O:4].[OH-].[Na+]>CO>[N:1]1([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:26][CH2:25][CH2:24][C@H:2]1[C:3]([NH:5][C@@H:6]([C:12]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[C:7]([S:10][CH3:11])([CH3:9])[CH3:8])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10814833HCID 10814833, compound

Product 1

HCID 10814358HCID 10814358, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Boc-Pro-DPen(Me)-Leu-OMe (0.94 g, prepared in Example (9-e)) in methanol (2.5 mL) was added 1N NaOH (2.5 mL) under ice-cooling. The mixture was stirred under ice-cooling for 30 min and at room temperature for 1 h. The mixture was evaporated under reduced pressure to remove methanol and water (20 mL) was added to the residue. The mixture was extracted with diethyl ether (20 mL). The aqueous layer was acidified with 10% aq. citric acid and extracted with ethyl acetate (10 mL×3). The combined ethyl acetate extracts were washed with brine (10 mL), dried over MgSO4 and evaporated under reduced pressure to give the product (0.94 g).

Workup

  1. temperaturecooling
  2. customThe mixture was evaporated under reduced pressure
  3. customto remove methanol and water (20 mL)
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with diethyl ether (20 mL)
  6. extractionextracted with ethyl acetate (10 mL×3)
  7. washThe combined ethyl acetate extracts were washed with brine (10 mL)
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d424795cdcbf4b0f8ded36512ca2d011
Source dataset
uspto-grants-1996_02
Patent number
US05494897

Reaction notes

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